Many organic compounds containing the trifluoromethyl group are extremely valuable compounds, useful in a variety of ways. For example, many agricultural chemicals which are herbicides, pesticides, and fungicides, contain the trifluoromethyl group attached to an aromatic ring. Perhaps one of the more famous is a herbicide sold under the trademark TREFLAN.RTM.. In addition, some well-known solvents have the trifluoromethyl moiety, as well as certain valuable chemical intermediates. In sum, there is a very real and continuing need for cheap, inexpensive and economic ways of introducing the trifluoromethyl group into both pharmaceutically active and agricultural chemically active compounds.
In the past, the synthetic routes for such compounds have been laborious. In particular, fluorinating agents used to prepare trifluoromethyl containing compounds have all been a compound which in fact already contained the trifluoromethyl group such as trifluoromethyl iodide, and bis(trifluoromethyl)mercury. These compounds are expensive, and not readily commercially available.
Contrasted with the expensive and difficult methods to obtain trifluoromethyl compounds, there are many cheap, commercially available difluorodihalomethanes, such as CF.sub.2 Cl.sub.2, CF.sub.2 BrCl, and CF.sub.2 Br.sub.2. However, no one has heretofore ever been able to achieve a direct synthesis of a trifluoromethyl organo metallic from a difluorodihalo methane compound.
Accordingly, it is a primary objective of the present invention to prepare trifluoromethyl organometallics from commercially available difluorodihalomethanes, such as dichlorodifluoromethane, chlorobromodifluoromethane, and dibromodifluoromethane.
Yet another objective of the present invention is to prepare trifluoromethyl organocadmium and zinc compounds from difluorodihalomethanes in a direct single step synthesis.
An even further objective of the present invention is to prepare stable trifluoromethyl copper reagents which are useful in further synthetic reactions to allow introduction of trifluoromethyl groups to other compounds.
A further objective of the invention is to prepare trifluoromethyl organometallic compounds of cadmium and zinc and copper which can be conveniently used to introduce the trifluoromethyl moiety to an olefinic derivative.
A further objective of the present invention is to prepare trifluoromethyl organometallic compounds of cadmium and zinc and copper which can be conveniently used to introduce the trifluoromethyl moiety into an aromatic compound.
A further objective of the present invention is to prepare trifluoromethyl organometallic compounds of cadmium and zinc and copper which can be conveniently used to introduce the trifluoromethyl moiety to an unsaturated organic compound, such as an acetylenic or an allylic compound.
A further objective of the present invention is to prepare trifluoromethyl organometallic compounds of cadmium and zinc and copper which can be conveniently used to introduce the trifluoromethyl moiety to an acyl derivative.
A further objective of the present invention is to prepare trifluoromethyl organometallic compounds of cadmium and zinc and copper which can be conveniently used to introduce the trifluoromethyl moiety for the preparation of other trifluoromethyl organometallics via metathesis reactions.
A still further objective is to prepare either directly or indirectly, perfluoroalkyl organometallic compounds of copper and other transition metals which can then be conveniently used to introduce a perfluoroalkyl group into an organic compound.
The method and manner of accomplishing each of the above objectives will become apparent from the detailed description of the invention which will follow hereinafter.